31 High Head Road South
Dennis, MA, 02660
$1,089,000
3 Beds
2 Baths
1,882 SqFt
0.35 Acres
Add
MLS #22600538 image #0MLS #22600538 image #1MLS #22600538 image #2MLS #22600538 image #3MLS #22600538 image #4MLS #22600538 image #5MLS #22600538 image #6MLS #22600538 image #7MLS #22600538 image #8MLS #22600538 image #9MLS #22600538 image #10MLS #22600538 image #11MLS #22600538 image #12MLS #22600538 image #13MLS #22600538 image #14MLS #22600538 image #15MLS #22600538 image #16MLS #22600538 image #17MLS #22600538 image #18MLS #22600538 image #19MLS #22600538 image #20MLS #22600538 image #21MLS #22600538 image #22MLS #22600538 image #23MLS #22600538 image #24MLS #22600538 image #25MLS #22600538 image #26MLS #22600538 image #27MLS #22600538 image #28MLS #22600538 image #29MLS #22600538 image #30MLS #22600538 image #31MLS #22600538 image #32MLS #22600538 image #33MLS #22600538 image #34MLS #22600538 image #35MLS #22600538 image #36MLS #22600538 image #37MLS #22600538 image #38MLS #22600538 image #39MLS #22600538 image #40MLS #22600538 image #41MLS #22600538 image #42MLS #22600538 image #43MLS #22600538 image #44MLS #22600538 image #45MLS #22600538 image #46MLS #22600538 image #47MLS #22600538 image #48MLS #22600538 image #49MLS #22600538 image #50MLS #22600538 image #51MLS #22600538 image #52MLS #22600538 image #53MLS #22600538 image #54MLS #22600538 image #55MLS #22600538 image #56MLS #22600538 image #57MLS #22600538 image #58
Tucked away on a quiet side street just up the hill from historic Route 6A, this remarkable East Dennis ranch offers the kind of location, setting, and lifestyle that rarely come together in one property. Moments from Cold Storage Beach, Sesuit Harbor, and Dennis Pines Golf Course, it sits within a coveted enclave of custom homes–an established executive neighborhood where no two houses are alike and pride of ownership is unmistakable.Lovingly held by one family and meticulously maintained, this home reveals itself slowly–and beautifully. From the outside, it feels classic and understated. Step inside, and the story unfolds in the most delightful way. The front portion of the home offers a gracious, traditional layout–warm, welcoming, and thoughtfully designed–while the rear addition opens into a bright, modern surprise. The transition is seamless, yet striking: timeless charm in the front, expansive and open in the back.The welcoming foyer opens to a sunken living room with tray ceiling and an expansive picture window that floods the space with natural light. From there, the layout flows into a generous dining room with views toward the sunroom beyond–creating a natural rhythm for entertaining and gathering.
The heart of the home is the expansive, beautifully updated white kitchen, complete with quality appliances, pantry, laundry area, and skylight. It opens effortlessly into a stunning family room with soaring ceilings, tile flooring, and walls of windows that invite the outdoors in. A generous kitchen peninsula transforms into a bar for eating or gathering, where guests can pull up a chair and stay connected to the action–whether it’s a casual breakfast, cocktails before dinner, or a lively Cape Cod evening with friends.
From here, glass doors lead into the extraordinary three-season room framed by beams and screens, capturing the spirit of Cape Cod living at its best. This is the room everyone dreams about–a place for morning coffee, long dinners, puzzles on rainy days, summer breezes, and memories that linger long after the season ends.
The design balances togetherness and privacy with intention. Bedroom spaces are thoughtfully tucked into their own wing, while the main living areas invite conversation, celebration, and the easy rhythm of coastal life. Every room feels generous, every space purposeful–ideal for hosting family and friends without ever feeling crowded.
Outside, a private backyard offers a peaceful haven for birds, blooms, and quiet reflection. It’s equally suited for cookouts, summer evenings under the stars, or simply enjoying the stillness of a Cape Cod afternoon.
This is not a cookie-cutter home–it’s a true surprise, a home that reveals depth, warmth, and remarkable living space the moment you step inside. It’s not fussy–it’s move-in ready, beautifully maintained, solid, and comfortable. The kind of home that simply feels right the minute you walk through the door.
Whether you’re a golfer, a boater, a beach walker–or all three–this is the kind of property where you drop your bags, grab your clubs, and leave your flip-flops by the door. Morning tee times. Afternoon swims at low tide. Sunset lobster rolls at the harbor. Ice cream on the ride home.
This isn’t just a house. It’s East Dennis, exactly the way it’s meant to be lived.

Property Details

Price:
$1,089,000
MLS #:
22600538
Status:
Pending
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Feb 21, 2026
Finished Sq Ft:
1,882
Total Sq Ft:
1,882
Lot Size:
15,246 sqft / 0.35 acres (approx)
Year Built:
1978
RanchWoodedDennis-yarmouth

Ask a Question

See this Listing

Send
  

Schools

School District:
Dennis-Yarmouth

Interior

Appliances
Dishwasher, Washer, Wall/Oven Cook Top, Washer/Dryer Stacked, Refrigerator, Gas Range, Microwave, Gas Dryer, Gas Water Heater
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Fireplaces Total
1
Flooring
Hardwood, Tile
Laundry Features
First Floor

Exterior

Architectural Style
Ranch
Construction Materials
Clapboard, Shingle Siding
Exterior Features
Outdoor Shower, Garden
Parking Features
Basement
Parking Spots
3
Roof
Asphalt, Shingle, Pitched

Financial

Tax Year
2025
Taxes
$3,711

Map

Community

Market Summary

Current real estate data for Single Family in Dennis as of Mar 21, 2026
53
Single Family Listed
118
Avg DOM
798
Avg $ / SqFt
$1,600,600
Avg List Price

Property Summary

    31 High Head Road South Dennis MA is a Single Family for sale in Dennis, MA, 02660. It is listed for $1,089,000 and features 3 beds, 2 baths, and has approximately 1,882 square feet of living space, and was originally constructed in 1978. The current price per square foot is $579. The average price per square foot for Single Family listings in Dennis is $798. The average listing price for Single Family in Dennis is $1,600,600. To schedule a showing of MLS#22600538 at 31 High Head Road South in Dennis, MA, contact your Pleasant Bay Realty agent at (774) 209-1428.

Similar Listings Nearby

broker reciprocity
MLS# 22600610broker reciprocity
23 Farm Lane South
Dennis, MA

$1,350,000

4.1 miles away

broker reciprocity
MLS# 22600200broker reciprocity
59 HOPE Lane
Dennis, MA

$1,200,000

1.5 miles away

broker reciprocity
MLS# 22600008broker reciprocity
36 Island Street East
Dennis, MA

$1,067,000

1.3 miles away

broker reciprocity
MLS# 22504920broker reciprocity
20 Spring Lane
Brewster, MA

$1,065,000

3.3 miles away

broker reciprocity
MLS# 22600697broker reciprocity
117 A P Newcomb Road
Brewster, MA

$995,000

2.3 miles away

broker reciprocity
MLS# 22503915broker reciprocity
4 Spadoni Way
Dennis, MA

$975,000

2.9 miles away

broker reciprocity
MLS# 22600753broker reciprocity
309 Great Fields Road
Brewster, MA

$950,000

3.6 miles away

broker reciprocity
MLS# 22600506broker reciprocity
12 Doves Wing Road South
Yarmouth, MA

$950,000

3.4 miles away

broker reciprocity
MLS# 22600756broker reciprocity
1 Shore Drive
Harwich, MA

$925,000

3.5 miles away

broker reciprocity
MLS# 22600474broker reciprocity
121 Eileen Street Port
Yarmouth, MA

$848,000

3.0 miles away

31 High Head Road South
Dennis, MA